500894-21-3

Upstream product

• 500894-20-2 ((2R,3R,4R,5S)-5-Benzyl-3,4-bis-benzyloxy-tetrahydro-furan-2-yl)-methanol 
• 1407180-88-4 1β-(2-bromobenzyl)-2,3,5-tri-O-(tert-butyldimethylsilyl)-1-deoxy-D-ribofuranose 
• 1407180-91-9 1β-benzyl-2,3,5-tri-O-(tert-butyldimethylsilyl)-1-deoxy-D-ribofuranose 
• 157363-84-3 1,2:5,6-dianhydro-3,4-di-O-benzyl-L-iditol 
• 591-51-5 phenyllithium 
• 960-16-7 tributylphenylstannane 

Relevant academic research and scientific papers

Synthesis of substituted benzyl homo-C-ribonucleosides and -nucleotides as carba analogues of phosphoribosylanthranilate

New 2-substituted benzyl C-ribonucleosides and -nucleotides were designed as carba analogues of phosphoribosylanthranilate, a key intermediate in tryptophan biosynthesis. The synthesis was based on the preparation of TBS-protected 2-bromobenzyl C-ribonucleoside 4a by addition of (2-bromobenzyl)magnesium bromide to ribonolactone followed by reduction and subsequent functional group transformations. Pd-catalyzed hydrogenation, cross-couplings, amination or hydroxylation, as well as lithiation followed by reaction with CO2 and amidations, gave a large series of 2-alkyl-, 2-(het)aryl, 2-amino, 2-hydroxy, 2-carboxy and 2-carbamoyl derivatives that were deprotected to afford free homo-C-ribonucleosides. Some of the title nucleosides were converted to 5'-O-phosphates. Novel benzyl C-nucleosides were designed and prepared as carba analogues of phosphoribosylanthranilate, an important intermediate in the biosynthesis of tryptophan. Copyright

Efficient access to ATP mimics, potential FGF receptor tyrosine kinase inhibitors

Nucleophilic opening of bis-epoxide 1 derived from D-mannitol by organolithium species in the presence of boron trifluoride etherate allows the synthesis of enantiopure polyhydroxy tetrahydrofurane skeletons with aromatic moieties in the pseudo-anomeric p